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Finding Your Dream Home: How to Choose the Perfect Luxury Property in Islamorada, FL

Finding Your Dream Home

This brand-new custom-built oceanfront resort-style home is one of many Islamorada luxury homes for sale. Inquire here.

A tropical paradise with purple sunsets, Islamorada is an enchanting place where people go on a vacation and end up finding their dream home. It is located on the southern coast of Florida and sits at the center of the Florida Keys. This vacation community is spread across six of Florida’s sunkissed Keys: Plantation Key, Upper Matecumbe Key, Lower Matecumbe Key, Windley Key, Indian Key, and Lignumvitae Key.

Islamorada is famous as the “Sport-fishing Capital of the World.” While only about 6,000 people reside in this 20-mile-long collection of islands, an impressive number of tournament-grade captains call the island home. Its waters are teeming with highly sought-after gamefish, such as sailfish, mahi-mahi, king mackerel, bonefish, redfish, tarpon, and permit.

There are many Islamorada luxury homes for sale suited to all kinds of preferences, lifestyles, and investment goals. So how does one find the perfect dream home in the “Purple Island”? Just keep these clear and practical steps in mind when choosing among the finest Islamorada real estate.


Caucasian couple drinking champagne and talking together while catamaran boat sailing at summer sunset

There are a million things to enjoy in the Fabulous Florida Keys, and relaxing is on top of that list. There is no doubt that being able to relax in the privacy of one’s own living space is the best way to experience downtime in Islamorada. That is why potential homebuyers should carefully discern which type of Islamorada real estate best suits their needs and preferences.

Why are you searching for an Islamorada home?

  • Holiday. Why stay at a hotel when one can have the comforts of a real home while enjoying all that Islamorada can offer? Having a holiday home saves people from the hassle of finding a base to explore Islamorada whenever they visit. A holiday property provides a more private and comfortable setting than staying in a hotel for an entire vacation. Owned or rented for leisure, Islamorada holiday homes can be houses, cabins, cottages, condominiums, or apartments.

    Browse available homes for sale in Islamorada

  • Rental. Those who want to enjoy the Keys repeatedly or require budget-friendly options for longer stays can benefit from rental properties. Since the area is a prime beach destination, there is an array of Islamorada luxury rentals available. Renters also often have the advantage of not having to pay property taxes or maintenance fees. Another benefit to renting in Islamorada is having access to amenities like a pool, a barbecue area, or a marina.

    Inquire about investing in a luxury rental property in Islamorada

  • Permanent. Buying a home in Islamorada is like owning a piece of paradise. In the Keys, vacation living isn’t something that’s enjoyed on occasion – it’s day-to-day life. It’s not uncommon to hear of people vacationing in Islamorada and then deciding to buy a permanent home in the community.

    A permanent home is a person’s primary residence intended for year-round use over a significant period of time. In Islamorada, a potential homeowner can choose among different types of permanent homes. There are luxury waterfront homes, single family homes, homes in gated communities, and upscale condominiums, with features that will suit young professionals, growing families, couples, or retirees.

    Browse available homes for sale in Islamorada

  • Secondary. Experiencing Islamorada’s laidback lifestyle will make anyone want to go back again and again. Those who can’t stay year-round often choose to have a second home they can return to whenever they want. But what is a secondary home and how is it different from a holiday home?

    A secondary home is an additional residence where one can spend weekends, holidays, or vacations. Unlike a holiday home which can be a time-share or a full-time rental, a secondary home can be used for year-round occupancy. Most people who have secondary homes in Islamorada often occupy the property during parts of the year that suit their schedule.

    Inquire about vacation homes for sale in Islamorada

  • Retirement. Who doesn’t want to retire in the warm and sunny shores of the Sunshine State? Islamorada has all the components of blissful living in the tropics, including retirement homes. Discovering new pastimes and enjoying island living is possible in the safe and maintenance-free setting of a retirement lodging.

    In the Keys, retirement communities often come with astounding views of the water. There are assisted-living and independent-living facilities that feature resort-style amenities and are close to world-class attractions. Home-care providers are also easy to find in Islamorada, which makes it perfect for retirees who want to live in their own permanent homes or senior apartments.

    Inquire about relocating to Islamorada


Luxury Living

The architectural styles found in Islamorada homes pay homage to the natural beauty of the islands, its rich history, and the diversity of its community.

  • Conch homes. An architectural treasure of the Keys, Conch homes are built in the Bahamian style made from wood by 19th-century shipbuilders. These brightly colored homes have wraparound verandas and shuttered windows.

  • Cigar cottages. These single-story cottages get their name from the Cuban cigar makers that built them in the late 19th century. A central hall that starts from the front door all the way to the back door is the main architectural feature of cigar cottages.

  • Mediterranean. Some of the newer properties in the Keys feature the Mediterranean style. These luxury mansions usually have white stucco exterior walls and red-tiled roofs. The thick walls help keep the interior cool during the summer months.

  • Modern. Islamorada’s modern homes are often built with top-tier luxury in mind. Floor-to-ceiling windows, open floor plans, and infinity pools make the most out of the panoramic views seen from waterfront properties.

  • Queen Anne. No other architectural style mirrors the magic of living in the Keys as much as Queen Anne. Like a home from a fairytale, these colorful houses feature large porches, cross gables, and steep roofs with ornate Victorian touches.

    Browse available homes for sale in Islamorada



Luxury homes aren’t a one-size-fits-all type of property. Every homebuyer has their own definition of what makes a property a luxurious home. Those who are looking for their Islamorada dream home should carefully consider the features and amenities they need for daily life.

Here’s how:
Make a list
To make real estate goals clearer, homebuyers should list down all the things they want in a property. From architectural styles to facilities, having a complete list can definitely pare down options and keep things focused. A list also makes it easier for a real estate agent to find the right property.

Look beyond the photos
Social-media worthy and Instagramable pictures of houses can be seen on listings everywhere. However, a potential buyer must always ask: Do the photos represent the actual state of the property or are they just for show? Potential homebuyers should take the time to visit and inspect the property to ensure that features and amenities are as advertised.

Consider future needs
Buying a luxury property can provide the space and flexibility to accommodate future plans. For example, couples who are thinking about settling down and starting a family should choose a home with extra rooms. Those who plan to host vacationing friends might look for a home with more space for entertaining. Retirees may need dedicated rooms to house their collections or pursue new hobbies.


Beautiful woman at home looking through the window on a rainy day enjoyng a cup of coffee

Luxury properties are often subject to safety and security considerations. Homeowners have a greater need to ensure that their sizable properties remain private and well-protected. Fortunately, a lot of Islamorada homes are now equipped with modern and versatile features to create a safe and secure space.

Gated communities
Perhaps the easiest way to ensure privacy and security is to choose a gated community. Some Islamorada luxury communities have modern gate access with 24-hour manned security. These features give homeowners control over who has access to their homes and also prevent unwanted visitors.

Smart home technology
Smart home technology like security cameras, smart keys, and smart lighting are now becoming the norm. Advanced security camera systems can monitor both the interior and exterior of a property, alerting homeowners to threats and providing recorded footage if needed. Smart keys are used to control access to the property instantly and remotely. Smart lighting with preset features or remote control can make it seem like a vacation home is occupied even when its residents are out and about.

Climate-resilient homes
Most luxury waterfront homes in the Keys are constructed using materials that can withstand the elements over a long period of time. Water-resistant materials and windows that won’t buckle under gale force winds have become permanent features that enhance the safety of a home. Homeowners can have peace of mind knowing that their property, their loved ones, and their belongings are protected from extreme weather.


young Family Walking in Winter Park Neighborhood Orlando Florida

A luxury property belongs in a luxury location. One of the most important things to consider when investing in Islamorada real estate is the neighborhood. The location of a home not only influences the value of a property, it also affects day-to-day life.

To help narrow down the property choices, explore different neighborhoods and areas in Islamorada. Do an extensive research of the neighborhood you’re interested in to determine:

Determine average property values
The average property values of a neighborhood can give potential homebuyers an idea how a home’s market price can appreciate over time. Look at the current and projected property values in the neighborhood and nearby locales. Take into account the community and lifestyle, neighborhood development, the quality of the school district, etc.

Meet the neighbors
It’s good to talk to interact with the people in the neighborhood to find out what they think of the community they live in. Their opinions offer valuable insight on the neighborhood itself along with its culture, interests, and dynamics. Lastly, talking to the neighbors will give buyers an idea if they’ll fit in.

Check out proximity to amenities, schools, and workplaces
Excellent access to local amenities, schools, and businesses is essential to living comfortably in a luxury property. Most of Islamorada luxury homes for sale have either private or public access to watercraft amenities, such as marinas, boat ramps, dry storage, and fishing supply shops – a must when living in the sport-fishing capital of the world.

The value of a property also increases if it’s located within a good school district. There are several top-rated public schools in Islamorada, such as Treasure Village Montessori Charter School, Plantation Key School, and Ocean Studies Charter School.

People who live in a vacation destination don’t want to spend a lot of time on non-leisure activities, including long commutes to work. Islamorada luxury rentals or homes that are close to work or business allow residents more time for fun and leisure.

Look into neighborhood perks

  • Islamorada neighborhoods have their own unique characteristics and features.
  • Angler’s Reef is best for fishing aficionados and those who value peace and privacy.
  • Great for families, Plantation Key Colony is a popular choice among those who want to be close to shops and schools.
  • Those who want amenities like hot tubs and tennis courts should consider the canalfront community of Sunshine Estates.


Successfully seal the deal on a luxury property by consulting with high-tier Islamorada real estate agents! An experienced Islamorada Realtor can provide invaluable help in finding the perfect luxury home in the Florida Keys. There are many benefits of working with experienced real estate agents like:

Step-by-step guidance
Purchasing luxury homes can be a long process. First-time buyers can benefit greatly from the help provided by Islamorada Realtors. The best Realtors will be with the buyer every step of the way to guide them, from search to closing.

More time to review options and deals
Working with a luxury Realtor can speed up the process because they already possess the tools, the experience, and the knowledge that buyers working alone would have to muddle through. Thus, a Realtor’s expertise allows buyers more time to consider all their options and not rush into decisions.

Negotiations can be handled by real estate agents
Negotiating the terms of a real estate purchase takes skill and patience, qualities Realtors are trained for. They can help craft offer letters, advise you on counter-offers, leverage market information, and shepherd a deal that will be fair to all concerned. In a competitive market like Islamorada, having an expert negotiate on your behalf definitely increases the chances of landing a dream property with favorable terms.

Experienced in dealing with luxury real estate
Buying a luxury home is different from purchasing regular property. Aside from the difference in price points, luxury homes come with more things to consider. Market trends and economic factors can significantly impact the luxury real estate market. Timing can be crucial for buying high-end properties. Advanced negotiation skills may be needed to handle high-value transactions and unique demands from sellers of luxury homes. And international buyers could pose a new set of legal and financial requirements. An experienced luxury real estate agent will be able to handle all that.

Access to exclusive listings
Some of the best luxury real estate can’t be found online at all. Sellers of luxury homes often want to maintain their privacy. When their properties go on the market, they are placed on exclusive listings that only the most experienced luxury Realtors know about. With their extensive connections in the local upscale market, luxury Realtors can help potential buyers access such listings which would otherwise have been unavailable for viewing.


There might be a lot of things to consider when buying Islamorada luxury homes for sale, but working with the right real estate professional can make the process hassle-free.Experienced Islamorada Realtors can easily provide all the needed information and options to make sure buyers are able to reach their real estate goals.

Angel DiGiorgio Florida Keys Luxury Real Estate has been providing personalized real estate services for over 25 years. Angel and her team are especially adept at managing luxury and high-end property transactions. With their impressive track record in Islamorada real estate, Angel and her team are also the go-to specialists for top-tier properties in nearby communities like Key Largo, Tevernier, Ocean Reef, Marathon, and Upper Keys.

Make your Islamorada dream home a reality by working with a dedicated Islamorada Realtor. Get in touch with Angel DiGiorgio Florida Keys Luxury Real Estate by calling 305.509.0971 or sending a message here.